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Tetracyanoquaterrylene and Tetracyanohexarylenequinodimethanes with Tunable Ground States and Strong Near-Infrared Absorption

Authors

  • Dr. Zebing Zeng,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
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  • Sangsu Lee,

    1. Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • José L. Zafra,

    1. Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
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  • Dr. Masatoshi Ishida,

    1. Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • Xiaojian Zhu,

    1. Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
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  • Zhe Sun,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
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  • Yong Ni,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
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  • Prof. Richard D. Webster,

    1. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore (Singapore)
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  • Prof. Run-Wei Li,

    1. Key Laboratory of Magnetic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201 (China)
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  • Prof. Juan T. López Navarrete,

    Corresponding author
    1. Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
    • Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
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  • Prof. Chunyan Chi,

    Corresponding author
    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
    • Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
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  • Prof. Jun Ding,

    Corresponding author
    1. Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
    • Department of Materials Science & Engineering, National University of Singapore, 119260 (Singapore)
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  • Prof. Juan Casado,

    Corresponding author
    1. Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
    • Department of Physical Chemistry, University of Malaga, Campus de Teatinos s/n 229071 Malaga (Spain)
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  • Prof. Dongho Kim,

    Corresponding author
    1. Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
    • Department of Chemistry, Yonsei University, Seoul 120-749 (Korea)
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  • Prof. Jishan Wu

    Corresponding author
    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
    2. Institute of Materials Research and Engineering, A*STAR, 3 Research Link, 117602, Singapore (Singapore)
    • Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore (Singapore)
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  • J.W. acknowledges the financial support from MOE Tier 2 grant (MOE2011-T2-2-130) and IMRE Core funding. The work at Yonsei Univ. was supported by WCU programs (R32-2010-10217-0) and an AFSOR/APARD grant (no. FA2386-09-1-4092). The work at Spain was supported by the Ministerio de Educación y Ciencia of Spain and by FEDER funds.

Abstract

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Biradicaloids based on quinoidal rylenes! Soluble and stable tetracyanoquaterrylenequinodimethane (QR-CN) and tetracyanohexarylenequinodimethane (HR-CN) were synthesized. QR-CN has a closed-shell quinoidal structure in the ground state, whereas HR-CN has a singlet biradical ground state. Both compounds showed very strong one-photon and two-photon absorption in the NIR range.

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